Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 14 days

Day 1: Arrive in Madrid, Evening Tapas Experience

Welcome to Spain! Upon arrival at the nation's capital, you'll enjoy a private transfer to your hotel in the city center. Take some time to settle in before heading out to explore highlights like the Puerta del Sol, one of the city's most historic and expansive plazas. There's also Madrid's famous Fountain of Cibeles, with its 18th-century sculpture depicting Cybele, the Greek goddess of fertility, riding in a chariot pulled by lions.

In the evening, you'll dig into Madrid's culture on a two-hour walking excursion that stops at some great tapas bars. On this walk, you'll visit Barrio Las Letras, which is known as the "literary quarter." This historic neighborhood in the city center was once home to Spanish literary legends like Cervantes and Quevedo. Besides visiting some historical sites around here, you'll also stop at Calle Huertas for a bite at one of the many tapas bars that line the street.

Day 2: Private City Walk, Discover Madrid's Royal Legacy

Enjoy a half-day walk in Madrid led by an expert local guide today. Madrid has a long history, and today the city adorns itself with that history in its architecture, public spaces, and culture. One area you'll visit is the Madrid de los Austrias. It was built in the 16th century during the reign of the Hapsburg Dynasty's first ruler, Charles I, and is home to one of the grandest plazas in Spain, the Plaza Mayor, which was once the heart of Old Madrid.

You'll also visit the Royal Palace, the official home of the Spanish monarchs until 1931. You'll explore both the grounds and interior of this 3,418-room monument, entering the parade ground, the chambers of Charles III, several salons, the Royal Chapel, and the Hall of the Crown, which displays Charles I's crown, scepter, and throne.

Later you could visit El Retiro Park, the green lung of Madrid, abounding with sculptures, fountains, and an artificial lake perfect for a boat trip. There are also must-visit gardens here, including the Jardín de Vivaces ("Garden of Vivacious Plants"), Jardines de Cecilio Rodríguez (inspired by the Andalusia region), and a garden home to over 4,000 roses. The best time to see these blooms is from May through June. 

Day 3: Pick up Rental Car & Drive to Toledo, City Walk

In the morning, you'll pick up your rental car and embark on your road trip through Spain. The first stop is the city of Toledo, located about an hour south of Madrid. Upon arrival, you'll check into your hotel, which features a breathtaking view of Toledo's city center. In the afternoon, you'll meet a local guide for a walk through this historic city, which enjoys a dramatic location atop a gorge overlooking the Río Tajo.

In the 16th century, Toledo was the capital of Spain. Back then, it was known as the "City of the Three Cultures," a place where—legend has it—Christian, Muslim, and Jewish communities peacefully coexisted. You can see remnants of this in the old Arab, Muslim, and Christian monuments that still stand. These include the 15th-century San Juan de los Reyes Monastery, the former Roman palace Alcázar de Toledo, and the Moorish Synagogue of Santa María la Blanca, which dates to the 12th century.

The tour includes stops at these historic landmarks as well as others, including the grand 13th-century Toledo Cathedral and the 12th-century Church of Santo Tomé. Throughout it all, you'll tour the ancient streets of an incredible city that could aptly be described as an open-air museum. After all, Toledo does enjoy UNESCO World Heritage status. 

Day 4: Drive to Almagro via Las Tablas de Daimiel

After an early breakfast at the hotel, you'll leave Toledo on a 1.5-hour drive south to the town of Almagro. You'll make a stop while passing through the arid plateau region of La Mancha. This was the home of the protagonist in Spain's most celebrated novel, "Don Quixote." He may have been a fictional character, but the windmills featured in that everlasting work by Cervantes are very real staples of La Mancha. It's also home to Tablas de Daimiel National Park, one of Spain's most important wetland ecosystems.

You'll meet an expert guide who will lead you on a four-hour excursion through Spain's smallest natural park, home to various migratory waterbirds, like herons and egrets, who flock to these expansive wetlands during winter. You'll walk along wooden pathways to the best vantage points for viewing nesting flocks in the last floodplain wetland in the central Iberian peninsula. After the tour, you'll continue to Almagro, where you'll check into your hotel.

Almagro may be small in scale, but it abounds with rich history and beautiful landmarks. Its well-preserved 15th-century architecture is a throwback to when Almagro was defined by its aristocratic culture, which you can see in the stately manor homes and grand Plaza Mayor, lined with colonnaded buildings. But the city is most famous for its 16th-century open air-theater, the Corral de Comedias. You can visit the Corral during the day or check the calendar to see if there's a show playing at night.

Day 5: Explore La Mancha, Drive to Valdepeñas

In the morning, you'll hop back in the car and enjoy a day trip around La Mancha. You'll have the freedom to design an itinerary according to your interests, but there are some highly recommended regional activities, such as a Manchego cheese workshop. This cheese is popular around the world, but many don't know that it hails from La Mancha. Made from the Manchego sheep's milk, it has a buttery texture and comes cured or semi-cured.

You'll visit a family-run farm where they still prepare Manchego the same way they did centuries ago. After touring the grounds and seeing the animals and facilities, you'll sit down for a hands-on lesson on how to make your own Manchego cheese. In the afternoon, venture to the beautiful Campo de Calatrava, a comarca (traditional region) of La Mancha known for volcanic hills and glassy lagoons.

This area was named after the military Order of Calatrava, who controlled the region in the 10th-12th centuries when La Mancha was the frontier between Christian and Muslim Spain. Here you can visit castles like Calatrava la Nueva and archaeological sites like Oreto and Zuqueca, home to the remains of a Visigoth cemetery and an ancient Muslim city. Then, continue to your hotel in the rural wine-producing region of Valdepeñas in southern La Mancha. 

Day 6: Wine Excursion in La Mancha

Today you'll explore Valdepeñas. Not only does this region enjoy the Designation of Origin (DO) mark of quality, but La Mancha is also the world's largest continuous wine-growing region with over 300 vineyards and 22,000 grape growers. With an expert guide, you'll learn about the different grape varieties grown in the region, the care and techniques that go into harvesting grapes on a small-production vineyard, and the external factors that can influence the quality of the grapes—everything from the weather to astrology. 

After visiting the vineyards, you'll see firsthand the enormous terracotta fermentation containers where the grapes become wine. Each one holds an impressive 1,585 gallons (6,000 liters). Now it's time to sample some wines. Popular varietals in La Mancha include Grenache and Tempranillo. 

Now it's time to eat. Feel free to choose where to enjoy a traditional La Mancha lunch, and we suggest Villanueva de los Infantes. With its early 17th-century Plaza Mayor (central plaza) and various medieval hermitages and convents, this throwback village is straight out of the mind of Cervantes. In fact, Villanueva de los Infantes is generally accepted to be the town referenced at the beginning of "Don Quixote" as the title character's home. 

Day 7: Drive to Mérida

This morning you'll once again hit the open road, driving about 3.5 hours west from La Mancha to the city of Mérida. This city is the capital of the Extremadura region of west-central Spain, and it has a historical legacy dating back to Roman times. After checking into your hotel, you'll have the remainder of the day free to relax.

Day 8: Guided Walk in Mérida

You'll begin the day by meeting a local expert guide who will lead you on a walk through the city. On this excursion, you'll visit Mérida's historic center, which features more extensive Roman ruins than anywhere else in Spain. Because of these archaeological sites, Mérida was declared World Heritage Site by UNESCO in 1986.

Mérida was founded as a Roman colony in the year 25 CE by Emperor Octavio Augustus. As the capital of the Roman province of Lusitania, it featured all the architectural hallmarks of a great city. Your guide will lead you to many of them, including the open-air Roman Theatre. Other impressive sites include the Puente Romano (stone bridge over the Guadiana River), the Circo Romano (ancient hippodrome), and the Casa del Mitreo, the remains of a Roman house with well-preserved frescoes. 

After the barbarians invaded in the 5th century, Mérida became the capital of the Visigoth Kingdom of Hispania. In 713, the city fell into Muslim hands, where it remained until the Christian reconquest in 1230. The outing includes entrance fees to all archaeological sites plus the National Roman Art Museum of Mérida. Afterward, you'll return to your hotel and have the remainder of the day free.

Day 9: Drive to Cáceres

Today you'll drive about an hour north from Mérida to the city of Cáceres, which is located in Extremadura. Upon arrival, you'll check into your hotel and then head out on a self-guided walk.

Like Mérida, Cáceres is another historic city with well-preserved Roman roots. It was founded by the Romans in 25 BCE, and after the end of the empire, it fell under the control of the Visigoths before the Moors conquered it in the 8th century. For hundreds of years during the Middle Ages, it changed hands between the Moors and Christians, and you'll see evidence of this history in architecture from Roman, Moorish, Northern Gothic, and Italian Renaissance.

After spending the day sightseeing, you can enjoy dinner in town. Cáceres is known for its great tapas and cutting-edge culinary scene.

Day 10: Old Town Cáceres Walk

After breakfast, you'll meet your guide for a guided stroll in Cáceres, a city with UNESCO World Heritage status. The walk focuses on the Ciudad Vieja (Old Town), encircled by defensive walls and home to over 30 defensive towers. You'll visit the Torre Bujaco, an Arab tower claimed by Ferdinand II of León in 1170 but retaken by the Moors in 1173. There are great views of the city skyline from the top.

Throughout the rest of the outing, you'll stroll the cobbled streets of the Ciudad Vieja and visit historic medieval palaces and fortified houses. All of this architecture reflects a city ruled by rival factions from the 14th through the 16th centuries. You'll also stop by the Plaza Mayor, one of Spain's most beautiful central plazas.

Day 11: Drive to Trujillo & Explore the Town

In the morning, you'll drive about a half-hour east to the historic town of Trujillo. After checking into your hotel, you'll meet an expert guide for a walk. This town dates back to Roman times, yet it's off the tourist trail. As you walk the cobbled streets with your guide, you'll learn all about Trujillo's rich historical legacy (the conquistador Francisco Pizarro was born here), plus a mix of Gothic, Moorish, Jewish, and Christian influences in the medieval buildings that stand to this day.

You'll visit the major sites in town, including the Plaza Mayor. This central plaza is a throwback to medieval times, and surrounding it are buildings and churches dating to the 15th and 16th centuries. In the center of the plaza, you'll find an equestrian statue of Francisco Pizarro. 

Up from the plaza is the Iglesia de Santa María la Mayor, the most important church in town. Dating to the 13th century, this Gothic church features two towers, from the top of which you'll enjoy town and countryside views. Inside, above the altar, are impressive 15th-century paintings in the Hispano-Flemish style. Naturally, the walk also includes a visit to Trujillo Castle, the 9th-century fortress that's perched on a hill overlooking the town. Afterward, you'll return to your hotel and will have the remainder of the day free.

Day 12: Day Trip to Monfragüe National Park

Within the Extremadura region of Spain lies Monfragüe, a national park in the valley of the Tagus River. Besides its natural beauty, Monfragüe is known for its exotic birdlife and abundance of wild animals. In the morning, you'll transfer to the park, where you'll meet an expert naturalist who will be your guide/driver for the day. They'll lead the way into Monfragüe in a 4WD vehicle on a guided safari.

With binoculars in hand, you'll travel through the park, stopping as your guide points out fauna like black vultures, Spanish imperial eagles, deer, river otters, foxes, and much more. The tour also includes stops at famous landmarks like Salto del Gitano, a prime viewpoint overlooking the valley, and Puente del Cardenal, a stone bridge running over the Tagus River.

You'll also stop at many other stunning viewpoints and, as a bonus, take a break for a picnic amid Monfragüe's unspoiled nature. Afterward, you'll leave the park and transfer back to your hotel.

Day 13: Drive to Madrid, Free Day

After breakfast, you'll hit the road again for the 2.5-hour drive back to Madrid. Upon arrival, check into your hotel and return your rental car. You'll then have the remainder of the day free to enjoy however you see fit.

You might want to take this time to do more sightseeing and visit any locales you missed your first time in Madrid. You could also head to the shopping district along Gran Vía and pick up souvenirs and gifts to take back home. In the evening, if you'd like to dine amid history, try dinner at Botín. This Madrid staple has the distinction of being the oldest restaurant in the world.

Day 14: Depart Madrid

It's time to say farewell. After a leisurely breakfast, a car will pick you up and transfer you to the airport, where you'll catch your flight home. This concludes your Spanish adventure. Adios!